Toluene → HCID 67541261, compound

Participants

Reaction Conditions

Reaction Steps

Toluene (30 ml) and H2O (10 ml) were added into a mixture of 4 (1.2 g, 3.43 mmol), 2 (3.27 g, 8.59 mmol), Pd(PPh3)4 (0.22 g, 0.17 mmol) and Na2CO3 (3.43 g, 34 mmol). The reaction mixture was stirred at 90° C. for 12 hours, cooled to room temperature, and then extracted with methylene chloride. The organic extracts were combined, washed with water, and dried over MgSO4. Upon evaporating off the solvent, the crude product was purified by gradient column chromatography on silica gel with hexane/methylene chloride 9:1 to 3:1 (v/v) to yield 5 (0.62 g, 34%) as a white powder. 1H NMR (400 MHz, CDCl3, 298 K): δ(ppm) 8.40-8.33 (dd, 2H), 8.30-8.28 (d, 1H), 8.21-8.35 (d, 1H), 7.88-7.76 (m, 2H), 7.56-7.40 (m, 5H), 7.33-7.20 (m, 2H), 4.14-4.09 (m, 4H), 2.46-2.37 (m, 2H), 1.10-0.90 (m, 12H).

Provenance & Evidence